Admirers of Andy Warhol and Philip Pearlstein have long been aware of the early, unlikely friendship between the prophet of Pop and the gimlet-eyed observational realist who stripped the human figure of all glamour or narrative implications. As the latter tells it, the acquaintance began in a way that already reflects the Andy we know: On the campus of the Carnegie Institute of Technology in Pittsburgh, now Carnegie Mellon University, a fellow student by the name of Warhola approached him because Pearlstein’s work had been published in Life magazine as the result of him winning a contest for high-school artists. The future Warhol asked, “How does it feel to be famous?” Pearlstein recalls his reply as, “It only lasted five minutes.” As we all know, Warhol later decreed that we should all have at least three times as much fame. In any case, the friendship continued when the two young artists moved to New York in 1949, rooming together on St. Marks Place. A little later, Warhol would be part of the wedding party when Pearlstein married another former Carnegie art student, Dorothy Cantor.

“Pearlstein|Warhol|Cantor: From Carnegie Tech to New York,” which was organized by the Andy Warhol Museum in Pittsburgh, where it was first shown before traveling in reduced form to New York, offered a delightful look back at three young artists working to find channels for their talents. The least familiar of them, of course, is Cantor, who stopped working as an artist in 1957—a shame, for her grayish explorations of the sweeping geometry of an unpeopled cityscape are remarkably affecting. It is as if the celebratory cool of Precisionism were subtly infused with the pessimistic overtones of pittura metafisica.

Many of the works by Warhol and Pearlstein were clearly school exercises, and it’s fascinating to witness the two painting the same male model in a life class—in a pair of works from 1948, Warhol opts for more tonal unity, Pearlstein for more sense of sculptural volume. Other works suggest that both artists were attracted to the incisive draftsmanship of Ben Shahn, though only Pearlstein was tempted by his topical subject matter: The young artist’s Street Fight, 1946–47, depicts a gang of white youths threatening a couple of black teenagers. By contrast, Warhol opts for a sweeter, goofier view of youth in his Kids on Swings, 1946. Perhaps more surprising is that Pearlstein tried out, early on, subjects that Warhol would later make his own—evidenced not only in his Superman, 1952, here represented by a photograph (it is in the collection of the Museum of Modern Art, New York), but in Dollar Sign, 1949–50.

Still, if one would have tried to predict from his early work the direction young Pearlstein would have been best advised to follow, it might have been his bent toward a deft, good-humored social observation imbued with enough formal quirkiness to make something more of it, as represented here by Art Class, 1946–47, which shows Warhol and a friend at work, and String Quartet, 1948–49. Who knows? If Pearlstein had followed this path, he might have become a sort of Nicole Eisenman avant la lettre.

Of course, that’s not how it turned out. Like Warhol, Pearlstein would devote much of the ’50s to commercial work, only coming into his own as a painter in the ’60s—now eschewing all that was fanciful, humorous, or overtly eccentric in his art. Yet his earlier works also make it easier to make sense of the fascination with the grotesque, the cultivation of an almost hallucinatory exaggeration that has become more important to his paintings over the decades. In several of the new works by Pearlstein that Betty Cuningham Gallery put on view alongside “Pearlstein|Warhol|Cantor” (all 2015, save for one dated 2013), nude models wear masks, allowing the empiricist to flaunt his love of unreality, while the distorted, congested space of other works confirm his own observation that his art is about “controlling hysteria.” Pearlstein’s empiricism turns out to have been the long back road to his own imagination.

—Barry Schwabsky